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These Boots Make All Of My Winter Outfits Look Cooler

They work with everything.

Originally Published: 
Karen walking in cowboy boots.
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For many years, when I thought of the perfect outfit, my vision never included shoes. It was all about the mixing and matching of the right clothing pieces, and more was more. A maximalist skirt matched with an equally playful top, or a cool graphic tee paired with a funky pair of trousers. Whatever it was, the clothing choice was the center of attention, and shoes were always an afterthought. I based the shoes on the outfit, not the other way around. That is, until the last few years. As my personal style has evolved I’ve come to appreciate a more curated closet — simpler, comfortable, clothing choices, upgraded by an amazing pair of shoes. And for winter, that equates to classic boots that truly make an outfit.

The power of a gorgeous pair of boots is unrivaled. They have the ability to take your look to another dimension — no matter how minimal that look might feel. While the bitter temps are not always welcome during fall and winter, the variety of boots that come in to save the day certainly is. Boots serve as the heart of cold-weather style, having the ability to completely alter an outfit and create that perfect look without relying on any other pieces.

During the winter months, I’m most concerned with staying warm and remaining comfortable in my daily sartorial choices. In fact, I often find myself wearing a slight variation of the same, streamlined ensemble most days: a well-fitted pair of jeans and a cropped cashmere sweater or a fitted turtleneck. Perhaps a pair of leggings and an oversized sweater. The beauty of it is, while the outfit is simple, I know I’m going to make a statement with my footwear choices. Effortless, functional, and stylish.

This season, I’m leaning into practical styles that offer comfort and convenience. However, don’t mistake practical with boring. The three boot styles I’m keeping on rotation this season are anything but. I’m mixing classic styles, some that are particularly on trend for 2023, and some that never really left the fashion stratosphere. For example, you can’t go wrong with a timeless Chelsea boot, but put a modern spin on them with a platform style. They’ll go with virtually every outfit in your wardrobe and give you instant cool-girl status — even when paired with leggings.

Ahead, shop my go-to boot picks (including my favorite Chelsea platforms!) that will completely upgrade your winter aesthetic.

Platform Chelsea Boots

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Chelsea boots are a foundational wardrobe staple, a basic all stylish women should own. I’ve been wearing them for as long as I can remember and still can’t let go of my favorite pair I’ve owned since I was 22. But this season the classic style has gotten an edgy upgrade, taking on a chunkier, platform silhouette. This style will still be my go-to choice all winter long, with its practical, thick sole and comfortable shape. Add some edge to a simple outfit with a colorful or ultra-chunky pair, or streamline your look when worn in a neutral tone like black or creme. Either way, you can’t go wrong with this wear-with-everything style.

Riding Boots

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I am SO here for the return of this popular 2000s style. For years I stared at my old riding boots collecting dust in my closet, wondering not if, but when they would come back in style (because as we know, fashion is cyclical — it was only a matter of time), and the day has finally arrived. Riding boots offer a beautifully sleek silhouette, quickly and effortlessly elevating any outfit. For a preppier leaning look, go full equestrian with a wider calf silhouette and buckles. For a more modern take, choose a sleek, fitted silhouette without hardware or buckles.

Cowboy Boots

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Cowboy boots are not new to the trend cycle (they’ve been popular over the last few years) and yet I am still obsessed. More than any other style, a western-inspired boot adds an unexpected twist to an otherwise understated outfit. They are a standout style that look good with every winter outfit combination, from leggings and a sweater to a cozy long-sleeve knit dress. With a pair of cowboy boots, you don’t even need to think about what you’re wearing, because whatever it is, you’re going to look like an It-girl.

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